Sodium Iodide → (R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

HRID 1496870노트

반응식

HRID 1496870 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1.CNCCNC.[I-:27].[Na+]>O1CCOCC1.C(Cl)Cl.[Cu]I>[I:27][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1

참가 물질

7

반응물 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 71238288(R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

생성물 1

HCID 71238317(R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-one수율 26.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

50 mg of Example 27 and 9 mg of copper (I) iodide were suspended in 300 μL dioxane under argon. 9.6 μL N,N′dimethylethylendiamine and 45 mg of sodium iodide were added and the mixture heated to 110° C. over weekend. The mixture was diluted with DCM and extracted with aqueous ammonia and water, the organic phase was subsequently concentrated in vacuo and the residual purified with HPLC (XbridgeC18; MeOH/water, TFA) to yield 15 mg yellow solid as Example 37.

후처리

  1. extractionextracted with aqueous ammonia and water
  2. concentrationthe organic phase was subsequently concentrated in vacuo
  3. customthe residual purified with HPLC (XbridgeC18; MeOH/water, TFA)

출처 및 근거

ORD 기록
ord-404176f67322467a8d9e4d43fa960add
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199937B2

반응 노트

불러오는 중…